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Bismuth(III) Bromide‐Catalysed Substitution of Benzyl Alcohols with Arylsulfonylmethyl Isocyanides: An Unexpected Access to Sulfinates
Author(s) -
Li HuiJing,
Wang Rui,
Gao Jing,
Wang YuanYuan,
Luo DongHui,
Wu YanChao
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201401173
Subject(s) - chemistry , bromide , bismuth , reactivity (psychology) , substitution (logic) , benzyl bromide , organic chemistry , cytotoxicity , medicinal chemistry , combinatorial chemistry , in vitro , catalysis , biochemistry , medicine , alternative medicine , pathology , computer science , programming language
A bismuth(III) bromide‐catalysed direct substitution of benzyl alcohols with arylsulfonylmethyl isocyanides affords sulfinates under mild acidic conditions. An unforeseen reversed reactivity was observed in this highly selective formation of sulfinates instead of the formation of the usually favoured sulfones. Cytotoxicity tests ( in vitro ) indicated that the sulfinates exhibit antibiotic activity against a human leukaemia cell line HL‐60, which would widen the structural diversity of this antitumour target and confirm the perspectives of further investigations.